(6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-1H-benzo[d]imidazol-4-yl)(pyridin 2-yl)methanone → 1-(6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-1H-benzo[d]imidazol-4-yl)-2-methyl-1-(pyridin-2-yl)butan-1-ol

HRID 1773729

Reaktionsgleichung

Reaktionsgleichung von HRID 1773729
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[O:20])[C:10]3[N:14]=[C:13]([O:15][CH2:16][CH3:17])[NH:12][C:11]=3[CH:18]=2)=[C:5]([CH3:27])[O:4][N:3]=1.[CH:28]([Mg]Br)([CH2:30][CH3:31])[CH3:29]>C1COCC1>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)([OH:20])[CH:28]([CH3:29])[CH2:30][CH3:31])[C:10]3[N:14]=[C:13]([O:15][CH2:16][CH3:17])[NH:12][C:11]=3[CH:18]=2)=[C:5]([CH3:27])[O:4][N:3]=1

Komponenten

4

Edukt 2

HCID 117601753(6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-1H-benzo[d]imidazol-4-yl)(pyridin 2-yl)methanoneHCID 178456030HCID 178456030, Verbindung

Produkt 1

HCID 1176017801-(6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-1H-benzo[d]imidazol-4-yl)-2-methyl-1-(pyridin-2-yl)butan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-1H-benzo[d]imidazol-4-yl)(pyridin-2-yl)methanone (20 mg, 0.055 mmol) was dissolved in dry THF (0.55 mL) under argon. Sec-butylmagnesium bromide (1.0 M in THF, 0.27 mL, 0.28 mmol) was added dropwise and the reaction was allowed to stir for 10 minutes. The reaction was quenched with water, concentrated and purified by reverse-phase HPLC to give 1-(6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-1H-benzo[d]imidazol-4-yl)-2-methyl-1-(pyridin-2-yl)butan-1-ol intermediate. Intermediate was taken up in 0.5 mL EtOH and 0.3 mL 4.0M HCl/dioxane and heated to 65° C. for 1 hr. Reaction was concentrated and purified by reverse phase HPLC to afford the desired product

Aufarbeitung

  1. customThe reaction was quenched with water
  2. concentrationconcentrated
  3. custompurified by reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3decefea2a9d4441a39c1d8d52110a8b
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255089B2

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